ROLEX DATEJUST 16030:When painted Roman numerals find themselves on a Datejust, it’s a Buckley. Named after a New York industry legend, these dials have always been rare birds but it wasn’t until the early 2000’s that the world woke up to their extraordinary beauty.

A Vintage Rolex Datejust is one of the few material items that you can both enjoy for the rest of your life and, when the day comes, pass down to the next generation to do the same. A watch like this is never out of place – from Irish car bombs on a NATO to boring C-suite meetings on a cordovan strap, it never fails to serve you well, impressing the tasteful.

Dialing back in, this example, with its crispy steel case, rugged engine turned bezel and immaculate grey Buckley dial further proves that less is more and there is still, after all of those years, value in vintage Rolex. This is one of my favorite watches and I know it’ll never disappoint.

ROLEX 1601:The grey sunburst Datejust, while extremely elusive, is one of those watches worth tracking down. Not only could we easily get lost in the beauty of the dial and the way it reacts to the light, but the endless strap pairing possibilities. Whether on a steel jubilee, butterscotch calf strap or burgundy crocodile, this dial will never fail to blow you away.

DESOTOS CHRONOGRAPH:Vintage manual wind chronographs with interesting dials are some of the most desirable watches on the market today. Regatta timers, sunburst texture, pulsation scales and, of course, panda’s are on top of the desirable world. These are the kinds of watches, if you can find them, that will steadily appreciate in the coming years; even after the mild wear of baseball games, bike riding and beer shotgunning. This example, with its beautiful gold plated case, crisp white dial and solid black subdials is just about all you could ask for – throw the red lollipop chronograph second hand in and now you’re just spoiled.

DUFONTE:This vintage Dufonte watch is exactly what I’m talking about when I tell you watch geeks that, if you wait long enough, you’ll stumble upon truly valuable watches that wont break the bank. In the watch world, we lose sight of what a dollar means and what it should return us – this Dufonte does the opposite. It balances independently bold design elements like twisted lugs and a fluted bezel with ease, creating a totally unique and beautiful aesthetic. Beyond that, it features killer broad dauphine hands and incredibly funky geometric numerals. While Dufonte may have gone on to produce some very underwhelming watches in the 70’s and 80’s, this three hander is a wonder. It’s infinitely cooler than most modern production watches 5 times its price and it’s my pleasure to offer it here!

CARTIER TORTUE:Designed by Louis Cartier himself in 1912, the Cartier Tortue actually predates the Tank. And while it might not get the attention of its sibling, it’s just as iconic and charming. It’s a smoother, rounder execution of Cartier’s clear passion for refined yellow gold watches with white roman dials and on the wrist, it has significant presence. This particular example is a ladies model from the 1980’s and its condition is absolutely immaculate – the original white dial is unstained and 18k yellow gold case unblemished. And although small watches experienced a brief fall from popularity, they are, without question, hotter than ever.

TUDOR SUBMARINER:While Rolex rarely took the opportunity to experiment with the Submariner under their own name, under Tudor, they had a blast. Take this reference 75090, for example – while its foundation is built on the classic recipe of a steel oyster bracelet, beefy case, rotating bezel and mercedes hands, it takes a leap in color and swaps the classic black for a new, stunning blue. It brings all of the punch of a classic Submariner and adds some attitude for a fraction of the price. I might not be a tool watch guy, but this is one we can all agree on!